This paper explores contested notions of the purpose of education and careers work. The research for the paper examines public sector employee reactions to notion of a psychological contract breach, when cuts in funding put their jobs and careers at risk. It argues that, in this environment, the search for career fulfilment can be marked by feelings of cruel optimism, wicked problems and broken expectations. The findings are then used to present the case for further research, firstly, to address the notion of possible selves, as individuals explore alternative identity affirming career opportunities; and secondly, the impact of changes in public policy on the processes of psychological contracting between students and staff in further and higher education.